Isopropanol → Diallyldimethylammonium chloride vinyl alcohol

HRID 379503

Reaction equation

HRID 379503 reaction equation
[C:1](OC=C)(=[O:3])[CH3:2].[ClH:7].Cl.N(C([C:20](=[NH:22])N)(C)C)=NC(C(=N)N)(C)C.[CH:23](O)([CH3:25])[CH3:24].[OH-].[Na+].[CH3:29][C:30](O)([CH3:32])C>[Cl-].C([N+](CC=C)(C)C)C=C.O>[Cl-:7].[CH2:24]([N+:22]([CH2:29][CH:30]=[CH2:32])([CH3:20])[CH3:1])[CH:23]=[CH2:25].[CH:1]([OH:3])=[CH2:2]

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 6386tert-ButanolHCID 7904Vinyl AcetateHCID 14798Sodium HydroxideHCID 763442,2'-Azobis(2-methylpropanimidamide) dihydrochloride

Product 1

HCID 86760082Diallyldimethylammonium chloride vinyl alcohol

Reagents, catalysts & solvents 2

HCID 33286Diallyldimethylammonium chlorideCatalystHCID 962WaterSolvent3×

Procedure

A solution of diallyldimethylammonium chloride (32.6 g of a 65 percent solution in water), vinyl acetate (10.53 g), and 2,2′-azobis(2-amidinopropane)dihydrochloride (0.64 g) in 2-methyl-2-propanol (60 g) and deionized water (60 g) was heated to 60° C. for 21 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction solution was poured into isopropanol (2 L) and stirred for at least 15 minutes. The solution was decanted from the precipitated polymer. The polymer was suspended in isopropanol (2 L), stirred for at least 15 minutes, and allowed to settle. After decanting, the polymer was suspended in isopropanol (2 L), stirred for at least 15 minutes, and allowed to settle. The washed polymer was dried in a forced-air oven at 70° C. to afford 11.5 g. To a solution of a portion of the washed polymer (5.5 g) in deionized water (100 mL) was added NaOH (0.15 g of a 50 percent aqueous solution). The solution was heated at 60° C. with stirring for 23.5 hours. The reaction solution was transferred to a Spectra/Por 1 dialysis membrane bag (molecular weight cutoff 6000 to 8000) and dialyzed against deionized water for at least 18 hours. The dialyzed polymer solution was dried in a forced-air oven at 70° C. to afford 4.5 g.

Workup

  1. customThe solution was decanted from the precipitated polymer
  2. stirringstirred for at least 15 minutes
  3. customAfter decanting
  4. stirringstirred for at least 15 minutes
  5. customThe washed polymer was dried in a forced-air oven at 70° C.
  6. customto afford 11.5 g
  7. temperatureThe solution was heated at 60° C.
  8. stirringwith stirring for 23.5 hours
  9. customThe reaction solution was transferred to a Spectra/Por 1 dialysis membrane bag (molecular weight cutoff 6000 to 8000)
  10. customdialyzed against deionized water for at least 18 hours
  11. customThe dialyzed polymer solution was dried in a forced-air oven at 70° C.
  12. customto afford 4.5 g

Sources & evidence

ORD record
ord-4414543e11b84326a3b1c23b71b8e6fa
Source dataset
uspto-grants-2001_10
Patent number
US06299868B1

Linked notes

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